CN110590765B - Structure, preparation and application of 2-thiazole formaldehyde-furfural Schiff base - Google Patents
Structure, preparation and application of 2-thiazole formaldehyde-furfural Schiff base Download PDFInfo
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- 238000002360 preparation method Methods 0.000 title abstract description 4
- 239000002262 Schiff base Substances 0.000 title description 11
- 239000013078 crystal Substances 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 239000000126 substance Substances 0.000 claims abstract description 7
- 238000002844 melting Methods 0.000 claims abstract description 3
- 230000008018 melting Effects 0.000 claims abstract description 3
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 3
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 8
- BTWNEJOURYOHME-UHFFFAOYSA-N 1,3-thiazol-2-ylhydrazine Chemical compound NNC1=NC=CS1 BTWNEJOURYOHME-UHFFFAOYSA-N 0.000 claims description 7
- SJKFLKIRZNZSCR-GNXRPPCSSA-N O1C(=CC=C1)\C=N\N=C\C=1SC=CN=1 Chemical compound O1C(=CC=C1)\C=N\N=C\C=1SC=CN=1 SJKFLKIRZNZSCR-GNXRPPCSSA-N 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 239000002994 raw material Substances 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 238000000227 grinding Methods 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 206010008342 Cervix carcinoma Diseases 0.000 claims description 3
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 3
- 201000010881 cervical cancer Diseases 0.000 claims description 3
- 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 claims description 3
- 201000005202 lung cancer Diseases 0.000 claims description 3
- 208000020816 lung neoplasm Diseases 0.000 claims description 3
- 201000001441 melanoma Diseases 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims 2
- 238000010532 solid phase synthesis reaction Methods 0.000 claims 2
- 238000001308 synthesis method Methods 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 6
- -1 2- ((E) -furan-2-ylmethylene) hydrazono Chemical group 0.000 abstract description 5
- 230000003287 optical effect Effects 0.000 abstract description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 3
- 230000001093 anti-cancer Effects 0.000 abstract 1
- 230000036961 partial effect Effects 0.000 abstract 1
- 150000004753 Schiff bases Chemical class 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 3
- 238000003746 solid phase reaction Methods 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 238000002965 ELISA Methods 0.000 description 1
- 108010019160 Pancreatin Proteins 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000002155 anti-virotic effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 238000012921 fluorescence analysis Methods 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 230000005918 in vitro anti-tumor Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000000990 laser dye Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052751 metal Chemical class 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229940055695 pancreatin Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- General Health & Medical Sciences (AREA)
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Abstract
The invention relates to the fields of organic synthesis, optical materials, pharmaceutical chemistry and the like, in particular to a structure, a preparation method and partial properties of a compound crystal; the compound is yellow strip-shaped crystal with melting point of 97.0-99.9 deg.C and molecular formula C 9 H 7 N 3 OS, chemical name: 2- ((E) -furan-2-ylmethylene) hydrazono) methyl) thiazole; the structure of the compound is detailed in the specification, and the compound has certain fluorescence property and anticancer activity.
Description
Technical Field
The invention relates to the fields of organic synthesis, optical materials, pharmaceutical chemistry and the like, and a target product is synthesized in one step by using a simpler method.
Background
At present, with the continuous progress of modern science and technology, people have more and more researches on fluorescence and the fluorescence properties of the fluorescence are also more and more deeply researched. The fluorescent substance is widely applied to the fields of dyes, organic pigments, optical brighteners, photo-oxidizers, coatings, chemical and biochemical marking analysis, solar collectors, anti-counterfeiting marks, medicine tracing, lasers and the like. The organic fluorescent material is mainly used in the current popular technologies, such as fluorescent probes, fluorescence analysis and the like, and is an indispensable material for optical electronic devices, DNA diagnosis, photochemical sensors, laser dyes and organic electroluminescent devices.
Schiff bases are mainly organic compounds containing characteristic groups (-RC ═ N-) of imine or azomethine, and are usually prepared by condensation of amine and active carbonyl. Schiff base compounds and metal complexes thereof have important application in the fields of medicine and pharmacology, catalysis, analytical chemistry, corrosion and photochromism. In the medical field, Schiff base has biological activities of bacteriostasis, sterilization, anti-tumor and antivirus; in the field of catalysis, complexes of cobalt, nickel and palladium of schiff bases have been used as catalysts; in the field of analytical chemistry, Schiff bases are used as good ligands and can be used for identifying and identifying metal ions and quantitatively analyzing the content of the metal ions; in the corrosion field, certain aromatic schiff bases are often used as corrosion inhibitors for copper; in the field of photochromism, certain schiff bases containing characteristic groups also have unique applications.
Disclosure of Invention
The invention relates to a compound which can be used as fluorescent material and anticancer drug, the appearance of the compound is yellow strip crystal, the melting point is: 97.0-99.9 deg.C, molecular formula C 9 H 7 N 3 OS, chemical name: 2- ((E) -furan-2-ylmethylene) hydrazono) methyl) thiazole, having the following structure:
1. and (3) structural identification:
elemental analysis showed that this compound has the formula C 9 H 7 N 3 OS, molecular weight 205.24; elemental analysis results (%): the experimental values of C,52.69, H,3.49, N,20.49, S, 15.66; calculated values: c52.67, H,3.44, N,20.47, S, 15.62; the analysis of the single crystal structure shows that the crystal belongs to an orthorhombic system, the space group is Pca21,
z4. related 1 The HNMR spectrum is shown in figure 1; FIG. 2 and FIG. 3 are a thermal ellipsoid crystal structure diagram and a crystal structure stacking diagram of the compound, respectively.
2. A synthetic method.
The method I is characterized in that: taking (E) -2- (hydrazono) thiazole and furfural as raw materials, and completing the preparation in one step in a proper organic solvent. The method comprises the following steps:
1) dissolving (E) -2- (hydrazono) thiazole in a proper organic solvent, adding furfural according to a certain substance amount ratio, and stirring or grinding at a certain temperature for several hours to perform reaction.
2) Filtering, and naturally volatilizing the filtrate to separate out yellow strip-shaped crystals which are target products; if solid phase reaction is adopted, the target product crystal can be obtained by recrystallization with a proper organic solvent after the reaction is finished.
The second method is characterized in that: taking (E) -2- (hydrazono) thiazole and furfural as raw materials, and completing the steps in a proper organic solvent in one step, wherein the steps are as follows:
1) dissolving furfural in a proper organic solvent, adding (E) -2- (hydrazono) thiazole according to a certain substance amount ratio, and stirring or grinding at a certain temperature for reaction for several hours.
2) Filtering, and naturally volatilizing the filtrate to separate out yellow strip-shaped crystals which are target products; if solid phase reaction is adopted, the target product crystal can be obtained by recrystallization with proper organic solvent after the reaction is finished.
The two above processes differ in the order of addition of the reactants, but the molar ratio of the reactants is between 1:4 and 4: 1.
The organic solvent (including the solvent for reaction and the solvent for recrystallization) in the above two methods is selected from: methanol, ethanol, acetonitrile, dichloromethane, chloroform, tetrahydrofuran, acetone, etc., and the reaction may be carried out without using an organic solvent, and the raw materials may be reacted directly (i.e., solid phase reaction).
Preferably, the reaction temperature is normal temperature or heating reflux, and the reaction method is stirring or grinding.
Preferably, the reaction time is selected from: 1-10 h.
The beneficial effects of the invention are: can synthesize more complex functional molecular materials by simpler steps and reactants.
3. Ultraviolet and fluorescent properties
The compound has three strong absorption peaks at the wavelengths of 230.0nm, 265nm and 342.0nm, and the ultraviolet spectrum is shown in figure 4; has strong fluorescence emission peak in 375.0-450.0nm range, and the fluorescence spectrum is shown in figure 5; this indicates that the compound has better fluorescence properties.
4. In vitro antitumor activity:
respectively digesting A549 lung cancer cell, A375 human malignant melanoma cell and HeLa cervical cancer cell in logarithmic phase with 0.25% pancreatin to obtain single cell containing 10%The culture solution of fetal bovine serum F12K is prepared to have a concentration of 1.25 × 10 7 One cell/L suspension of single cells, cells were seeded in 96-well plates at 200. mu.L per well (2.5X 10 per well) 3 Individual cells). Place 96-well cell culture plates in CO 2 In an incubator at 37 ℃ with 5% CO 2 Culturing for 48h under the condition.
When the cells in the wells are full (90% full), adding different doses of the Schiff base solution (200 muL/well) according to experimental groups to make the final concentration of the compound to be detected respectively 25 muM, 50 muM, 100 muM, 200 muM, 400 muM and 800 muM, setting 3 multiple wells in each group, and culturing for 96 h.
mu.L of MTT at a concentration of 0.5g/L was added to each well, and the culture was continued for 4 hours to reduce MTT to Formazan (Formazan). After all the supernatants were aspirated, 200. mu.L of DMSO was added to each well, and the mixture was shaken for 15min to dissolve formazan sufficiently, and then absorbance (OD value) at 490nm was measured using an ELISA detector. Then calculated according to the following formula:
percent cell inhibition (control OD value-experimental OD value)/control OD value × 100%
Test results show that IC50 (half inhibition concentration of the drug) of the Schiff base on A549 lung cancer cells, A375 human malignant melanoma cells and HeLa cervical cancer cells is 780, 550 and 760 mu mol/L respectively, and the compound has weak inhibition effects on the three cancer cells.
Detailed Description
In order to better understand the present invention, the following embodiment further illustrates the technical solution of the present invention:
example 1
0.1270g (about 1mmol) of (E) -2- (hydrazono) thiazole was weighed out and dissolved in 50ml of acetonitrile, and the solution was put into a flask, stirred on a constant temperature heating magnetic stirrer, 166. mu.L (about 2mmol) of furfural was added to the solution by sucking with a pipette, and stirred under reflux for 2 hours. Gradually changing the solution into yellow brown, filtering after the reaction is finished, standing the filtrate, and naturally volatilizing; strip-shaped yellow crystals are precipitated at the bottom of the beaker, namely the target product, and the yield is about 87%.
Drawings
FIG. 1 is a 2- ((E) - (((E) -furan-2-ylmethylene) hydrazono) methyl) thiazole 1 HNMR spectrogram (DMSO-D) 6 )。
FIG. 2 is a crystal structure diagram of 2- ((E) -furan-2-ylmethylene) hydrazono) methyl) thiazole.
FIG. 3 is a graphic representation of the crystal structure of 2- ((E) - (((E) -furan-2-ylmethylene) hydrazono) methyl) thiazole.
FIG. 4 is a UV spectrum of 2- ((E) - (((E) -furan-2-ylmethylene) hydrazono) methyl) thiazole (10) - 5 mol/L,CH 2 CL 2 )。
FIG. 5 is a fluorescence spectrum of 2- ((E) - (((E) -furan-2-ylmethylene) hydrazono) methyl) thiazole (10) - 5 mol/L,CH 2 CL 2 )。
Claims (3)
1. A compound which appears as yellow stripe crystals with a melting point: 97.0-99.9 deg.C, molecular formula C 9 H 7 N 3 OS, chemical name: 2- ((E) - (((E) -furan-2-ylmethylene) hydrazono) methyl) thiazole, having the structure:
the crystal belongs to an orthorhombic system, the space group is Pca21,
Z＝4。
2. a method of synthesis of a compound as claimed in claim 1, characterized in that: the (E) -2- (hydrazono) thiazole and the furfural are used as raw materials, and a liquid phase synthesis method or a solid phase synthesis method can be adopted:
1) if a liquid phase synthesis method is adopted, dissolving all (E) -2- (hydrazono) thiazole in methanol, ethanol, acetonitrile, dichloromethane, chloroform, tetrahydrofuran or acetone organic solvents, adding furfural according to the mass ratio of 1:4 to 4:1, stirring for 1-10 h at normal temperature or at the reflux temperature, filtering, and naturally volatilizing the filtrate to separate out yellow strip crystals which are target products;
2) if the solid-phase synthesis method is adopted, the two reaction raw materials are mixed according to the mass ratio of 1:4 to 4:1, then grinding reaction is carried out for 1-10 h at normal temperature, and then methanol, ethanol, acetonitrile, dichloromethane, chloroform, tetrahydrofuran or acetone organic solvent is used for recrystallization, thus obtaining the target product crystal.
3. Use of a compound as claimed in claim 1, or a pharmaceutically acceptable salt thereof, for the manufacture of a medicament for the treatment of tumours, wherein: the tumor is lung cancer, malignant melanoma or cervical cancer.
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| CN110172337A (en) * | 2019-05-30 | 2019-08-27 | 南京师范大学 | A kind of benzothiazole derivant fluorescence probe and its preparation method and application |
| CN110229119A (en) * | 2019-05-21 | 2019-09-13 | 辽宁科技大学 | A kind of synthesis and application method of the benzothiazole bis-Schiff base fluorescent molecular probe for iron ion detection |
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| CN110229119A (en) * | 2019-05-21 | 2019-09-13 | 辽宁科技大学 | A kind of synthesis and application method of the benzothiazole bis-Schiff base fluorescent molecular probe for iron ion detection |
| CN110172337A (en) * | 2019-05-30 | 2019-08-27 | 南京师范大学 | A kind of benzothiazole derivant fluorescence probe and its preparation method and application |
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| Title |
|---|
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| "Synthesis and Biological Evaluation of Benzo[d]isothiazole，Benzothiazole and Thiazole Schiff Bases";Paola Vicini等;《Bioorganic & Medicinal Chemistry》;20031231(第11期);全文 * |
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